Gas chromatography of amino acids

Hušek, Petr; Macek, Karel

doi:10.1016/s0021-9673(00)86962-9

Cited by 159 publications

(39 citation statements)

References 321 publications

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“…GC analysis of amino acids and their metabolites requires esterification of the carboxyl group and acylation or alkylation of the amino group to make amino acids volatile and thermally stable (36). Furthermore, introduction of electron-capturing fluorine atoms into amino acid molecules by the use of perfluorated derivatization agents such as PFPA or HFBA renders the resulting derivatives highly electron-capturing.…”

Section: Identification Of 3-nt and Determination Of Basal 3-nt Levelmentioning

confidence: 99%

“…For quantification of 3-nitrotyrosine, the n-propyl ester-N-PFP-TMS ether derivative was selected. The n-propyl ester offers the advantage of higher stability to hydrolysis compared to the n-methyl ester (36). Subsequent conversion of the phenolic hydroxyl group of 3-nitrotyrosine to its TMS ether derivative ]tyrosine was monitored as the ion m/z 382.…”

Section: Identification Of 3-nt and Determination Of Basal 3-nt Levelmentioning

confidence: 99%

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Gas Chromatographic–Tandem Mass Spectrometric Quantification of Free 3-Nitrotyrosine in Human Plasma at the Basal State

Schwedhelm

Tsikas

Gutzki

et al. 1999

Analytical Biochemistry

125

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Section: Identification Of 3-nt and Determination Of Basal 3-nt Levelmentioning

confidence: 99%

Section: Identification Of 3-nt and Determination Of Basal 3-nt Levelmentioning

confidence: 99%

Gas Chromatographic–Tandem Mass Spectrometric Quantification of Free 3-Nitrotyrosine in Human Plasma at the Basal State

Schwedhelm

Tsikas

Gutzki

et al. 1999

Analytical Biochemistry

125

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“…Many derivatization procedures have been developed employing various reagents and various reaction conditions. Silylation is used for aliphatic hydroxyacids, dicarboxylic acids, ketoacids and AAs [27]. AAs yield two derivatives, as the carboxy group is silylated more readily than the amino group.…”

Section: Introductionmentioning

confidence: 99%

An evaluation of GC‐MS and HPLC‐FD methods for analysis of protein binders in paintings

Přikryl

Havlíčková

Pacáková³

et al. 2006

J of Separation Science

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Two chromatographic methods have been compared for analysis of protein-binding media used in paintings, namely, HPLC with fluorescence detection and GC-MS. The proteins were hydrolyzed to the corresponding amino acids (AAs) by gaseous HCl and the AAs were derivatized with methyl chloroformate, followed by GC-MS or by HPLC after derivatization with the AccQ fluorescence reagent. The hydrolysis, derivatization reactions and the chromatographic procedures have been optimized and applied to standard binding media, model and real samples of paintings. The methods have been compared and critically evaluated.

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“…Among the different reaction conditions reported in the literature ( The selection of the most useful anhydrides for the quantitative GC determination of amino acids is based on the published techniques concerning the two-step perfluoroacylation esterification procedure: these results indicate trifluoroacetic (TFAA) and heptafluorobutyric (HFBA) anhydrides. 54,55 The best results were obtained with HFBA, which is a strong acylating agent similar to TFAA, but it is more reactive and forms more stable derivatives than TFAA. 56 TFAA and HFBA were used in combination with the corresponding perfluorinated alcohols TFE (2,2,2-trifluoro-1-ethanol) and HFB (2,2,3,3,4,4,4-heptafluoro-1-butanol) to give three varieties of amino acid derivatives (Fig.…”

Section: Resultsmentioning

confidence: 99%

GC‐MS analysis of amino acid enantiomers as their N(O,S)‐perfluoroacyl perfluoroalkyl esters: Application to space analysis

et al. 2006

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The target of the in-situ research of optical activity in extraterrestrial samples stimulated an extended investigation of a GC-MS method based on the derivatization of amino acids by using a mixture of perfluorinated alcohols and perfluorinated anhydrides. Amino acids are converted to their N(O,S)-perfluoroacyl perfluoroalkyl esters in a single-step procedure, using different combinations of the derivatization reagents trifluoroacetic anhydride (TFAA)-2,2,2-trifluoro-1-ethanol (TFE), 2,3,3,4,4,, and heptafluorobutyric anhydride (HFBA)-HFB. The derivatives obtained are analyzed using two different chiral columns: Chirasil-L-Val and g-cyclodextrin (Rt-g-DEXsa) stationary phases which show different and complementary enantiomeric selectivity. The mass spectra of the derivatives are studied, and mass fragmentation patterns are proposed: significant fragment ions can be identified to detect amino acid derivatives. The obtained results are compared in terms of the enantiomeric separation achieved and mass spectrometric response. Linearity studies and the measurement of the limit of detection (LOD) show that the proposed method is suitable for a quantitative determination of enantiomers of several amino acids. The use of the programmed temperature vaporiser (PTV) technique for the injection of the untreated reaction mixture is a promising method for avoiding manual treatment of the sample and decreasing the LOD. KEY WORDS: chirality; amino acids; derivatization; GC-MS; in-situ analysis; planetary explorationThe in-situ search for organic molecules in extraterrestrial environments has been proposed for a better understanding of the solar system origin and the emergence of life on Earth. With this aim, detection of chemical biomarkers, i.e., of organic molecules that play an important role in biochemistry, will be one of the main goals of future space missions. Among the key chemical biomarkers on Earth, 1-3 amino and carboxylic acids which have been synthesized by experimental simulations under plausible prebiotic conditions, 4-6 have been detected in several meteorites 7-13 and in the lunar soil. 14-16 Thus, these chemical species appear to be widespread in the solar system, but they can exist without the presence of life. For this reason, the analysis of their optical activity seems to be a good complementary diagnostic tool to identify the link to a biotic or a prebiotic activity. In fact, almost exclusively L-amino acids are incorporated into proteins during microbial biosynthesis, although various D-amino acids have been found in archaea, yeasts, fungi, plants, insects, mollusks, and other eucaryotic organisms. [17][18][19] Because there are no evident biochemical reasons why L-amino acids should be selected over D-amino acids, it is generally assumed that life elsewhere could be based on either L-or D-amino acids, but not both. [20][21][22] Identifying an excess of D-amino acids in an extraterrestrial sample could provide unambiguous evidence for life that evolves independently from the Earth. [23][24] I...

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Gas chromatography of amino acids

Cited by 159 publications

References 321 publications

Gas Chromatographic–Tandem Mass Spectrometric Quantification of Free 3-Nitrotyrosine in Human Plasma at the Basal State

Gas Chromatographic–Tandem Mass Spectrometric Quantification of Free 3-Nitrotyrosine in Human Plasma at the Basal State

An evaluation of GC‐MS and HPLC‐FD methods for analysis of protein binders in paintings

GC‐MS analysis of amino acid enantiomers as their N(O,S)‐perfluoroacyl perfluoroalkyl esters: Application to space analysis

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